Prior to 2000, Jessica served as Vice President for Marketing and Communications at the National Council on Economic Education and the New York City chapter of the American Cancer Society.

Jessica spent most of her career in the art world. She was the Communications Director at The Museum of Modern Art; and held similar positions at The Solomon R. Guggenheim Museum and The New Museum of Contemporary Art in New York. Other related experience includes the San Francisco Museum of Modern Art, the San Francisco Art Institute, and Artweek magazine (Oakland).